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Name	5-[3-(Methylamino)propyl]-5H-dibenz[b,f]azepine hydrochloride	EINECS	200-373-1
CAS No.	58-28-6	Density	N/A
PSA	15.27000	LogP	4.79070
Solubility	H₂O: 50 mg/mL	Melting Point	214-216°C
Formula	C₁₈H₂₃ClN₂	Boiling Point	407.4 °C at 760 mmHg
Molecular Weight	302.847	Flash Point	160.5 °C
Transport Information	UN 1230 3/PG 2	Appearance	white to off-white powder
Safety	S7; S16; S36/37S45; S26; S24; S22	Risk Codes	R22; R36/37/38; R42/43; R48/23/24/25; R11
Molecular Structure		Hazard Symbols	Xn F T
Synonyms	5H-Dibenz[b,f]azepine,10,11-dihydro-5-[3-(methylamino)propyl]-, monohydrochloride (8CI);5H-Dibenz[b,f]azepine-5-propanamine, 10,11-dihydro-N-methyl-, monohydrochloride(9CI);10,11-Dihydro-5-[3-(methylamino)propyl]-5H-dibenz[b,f]azepinemonohydrochloride;5-[3-(Methylamino)propyl]-5H-dibenz[b,f]azepinehydrochloride;DMI hydrochloride;Demethylimipramine hydrochloride;Desimipramine-hydrochloride;Desipramine hydrochloride;Desipraminemonohydrochloride;Desmethylimipramine chloride;Desmethylimipraminemonohydrochloride;Desmethylimipramine-hydrochloride;GMI;JB8181;N-(g-Methylaminopropyl)iminodibenzylhydrochloride;Norpramin;Nortrimil;Pertofran;Pertofrane;

5-[3-(Methylamino)propyl]-5H-dibenz[b,f]azepine hydrochloride Synthetic route

: 58-28-6
desipramine hydrochloride

: 5231-87-8
3,4-diethoxy-3-cyclobuten-1,2-dione

: 131589-04-3
4-<<3'-(10'',11''-Dihydro-5H-dibenzazepin-5''-yl)propyl>(methyl)amino>-3-ethoxy-3-cyclobutene-1,2-dione

Conditions

Conditions	Yield
With triethylamine In ethanol for 5h; Ambient temperature;	100%

: 51146-56-6
(S)-ibuprofen

: 58-28-6
desipramine hydrochloride

: (S)-N-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-2-(4-isobutylphenyl)-N-methylpropanamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;	97%

: 106-31-0
butanoic acid anhydride

: 58-28-6
desipramine hydrochloride

: N-butyryldesipramine

Conditions

Conditions	Yield
With pyridine In toluene for 1h; Heating;	95%

: 126-00-1
4,4-bis(4-hydroxyphenyl)valeric acid

: 58-28-6
desipramine hydrochloride

: N-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-4,4-bis(4-hydroxyphenyl)-N-methylpentanamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;	82%

: 58-28-6
desipramine hydrochloride

: 88574-06-5
6-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}hexanoic acid

: (9H-fluoren-9-yl)methyl (6-((3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)(methyl)amino)-6-oxohexyl)carbamate

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;	80%

: 58-28-6
desipramine hydrochloride

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

A: N-Formyldesipramine

B: N-[3-(2-formyl-10,11-dihydro-dibenzo[b,f]azepin-5-yl)-propyl]-N-methyl-formamide

Conditions

Conditions	Yield
With trichlorophosphate at 95℃; Formylation; Vilsmeier reaction;	A 22% B 72%

: 143-66-8
sodium tetraphenyl borate

: 58-28-6
desipramine hydrochloride

: C18H22N2*C24H20B(1-)*H(1+)

Conditions

Conditions	Yield
In ethanol at 78℃;	68%

: 124-38-9
carbon dioxide

: 58-28-6
desipramine hydrochloride

: (3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)(methyl)carbamic fluoride

Conditions

Conditions	Yield
With dmap; diethylamino-sulfur trifluoride In acetonitrile at 25℃; under 760.051 Torr; for 2h; Schlenk technique;	64%

: 110-99-6
2,2'-oxybis-acetic acid

: 58-28-6
desipramine hydrochloride

: 1423770-96-0
2,2’-oxybis(N-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-N-methylacetamide)

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Inert atmosphere;	62%

: 1111-72-4
carbon dioxide

: 58-28-6
desipramine hydrochloride

: (3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)(methyl)carbamic fluoride-[13C]

Conditions

Conditions	Yield
With dmap; diethylamino-sulfur trifluoride In acetonitrile at 25℃; under 760.051 Torr; for 2h; Schlenk technique;	62%

5-[3-(Methylamino)propyl]-5H-dibenz[b,f]azepine hydrochloride Chemical Properties

Molecular Structure of 10,11-Dihydro-5-(3-(methylamino)prop-yl)-5h-dibenz(b,f)azepine hydro-chloride (CAS NO.58-28-6):

IUPAC Name: 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N-methylpropan-1-amine hydrochloride
Empirical Formula: C₁₈H₂₃ClN₂
Molecular Weight: 302.8416
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 4
Polar Surface Area: 6.48 Å²
Flash Point: 160.5 °C
Enthalpy of Vaporization: 65.93 kJ/mol
Boiling Point: 407.4 °C at 760 mmHg
Vapour Pressure: 7.56E-07 mmHg at 25°C
Melting point: 214-216°C
Storage temp: 2-8°C
Solubility: H₂O: 50 mg/mL
Form: powder
Color: white to off-white
InChI
InChI=1/C18H22N2.ClH/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20;/h2-5,7-10,19H,6,11-14H2,1H3;1H
Smiles
N1(c2c(CCc3c1cccc3)cccc2)CCCNC.Cl
EINECS: 200-373-1
Product Categories: Intermediates & Fine Chemicals; Pharmaceuticals; Biogenic Amine Transport Inhibitors; Biogenic Amine Transport InhibitorsObesity Research; Neurotransmission; Neurotransmission (Obesity); Neurotransmitters;Adrenoceptor

5-[3-(Methylamino)propyl]-5H-dibenz[b,f]azepine hydrochloride Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	intravenous	25mg/kg (25mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
guinea pig	LDLo	intravenous	55mg/kg (55mg/kg)	CARDIAC: OTHER CHANGES	Therapie. Vol. 20, Pg. 67, 1965.
man	TDLo	oral	490ug/kg (0.49mg/kg)	BEHAVIORAL: SLEEP	Journal of Clinical Psychiatry. Vol. 47, Pg. 210, 1986.
man	TDLo	oral	5mg/kg/5D-I (5mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: TOXIC PSYCHOSIS	American Journal of Psychiatry. Vol. 142, Pg. 386, 1985.
mouse	LD50	intraperitoneal	88mg/kg (88mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
mouse	LD50	intravenous	37mg/kg (37mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: REGIDITY	International Journal of Neuropharmacology. Vol. 4, Pg. 111, 1965.
mouse	LD50	oral	315mg/kg (315mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
rat	LD50	intraperitoneal	55mg/kg (55mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
rat	LD50	intravenous	19mg/kg (19mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 70, 1972.
rat	LD50	oral	871mg/kg (871mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 33, Pg. 1411, 1983.
women	TDLo	oral	14mg/kg/1W-I (14mg/kg)	KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED	Journal of Clinical Psychiatry. Vol. 44, Pg. 153, 1983.
women	TDLo	oral	36mg/kg/6D-I (36mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION	Journal of Clinical Psychiatry. Vol. 53, Pg. 160, 1992.
women	TDLo	oral	45mg/kg (45mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA	Annals of Pharmacotherpy. Vol. 27, Pg. 572, 1993.
women	TDLo	oral	70mg/kg/4W-I (70mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: TOXIC PSYCHOSIS	American Journal of Psychiatry. Vol. 142, Pg. 386, 1985.

5-[3-(Methylamino)propyl]-5H-dibenz[b,f]azepine hydrochloride Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Human systemic effects by ingestion: decreased urine volume, sodium level changes, chlorine level changes. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of NO_x and HCl.
Hazard Codes: Harmful Xn, Toxic T, Flammable F
Risk Statements: 22-36/37/38-42/43-48/23/24/25-23/24/25-11
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
R42/43:May cause sensitization by inhalation and skin contact.
R48:Danger of serious damage to health by prolonged exposure.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
R11:Highly flammable.
Safety Statements: 7-16-36/37-45-26-24-22
S7:Keep container tightly closed.
S16:Keep away from sources of ignition.
S36/37:Wear suitable protective clothing and gloves.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S24:Avoid contact with skin.
S22:Do not breathe dust.
RIDADR: UN 1230 3/PG 2
WGK Germany: 3
RTECS: HO0525000

5-[3-(Methylamino)propyl]-5H-dibenz[b,f]azepine hydrochloride Specification

10,11-Dihydro-5-(3-(methylamino)prop-yl)-5h-dibenz(b,f)azepine hydro-chloride , with CAS number of 58-28-6, can be called 10,11-dihydro-5-(3-(methylamino)propyl)-5h-dibenz(b,f)azepinehydrochloride ; demethylimipraminehydrochloride ; desmethylimipraminehydrochloride ; dmihydrochloride ; f)azepine,10,11-dihydro-5-(3-(methylamino)propyl)-5h-dibenz(hydrochlorid ; f)azepine,10,11-dihydro-5-(3-(methylamino)propyl)-5h-dibenz(monohydrochlor . It is a white to off-white powder, 10,11-Dihydro-5-(3-(methylamino)prop-yl)-5h-dibenz(b,f)azepine hydro-chloride (CAS NO.58-28-6) can be used as a more potent inhibitor of the norepinephrine transporter than the serotonin transporter.

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